Ali Siddiq: The Custom Fit Tour LIVE at Chesapeake Employers Insurance Arena
About the Performer
Ali Siddiq is one of the most compelling voices in stand-up comedy today. A Houston native, Siddiq’s comedy is rooted in raw, honest storytelling — drawing from his real-life experiences, including time spent incarcerated, to craft deeply personal and hilarious narratives that resonate with audiences across the country.
Known for his sharp wit, magnetic stage presence, and ability to tackle heavy subjects with humor and grace, Ali Siddiq has built a massive following through his Netflix specials, viral clips, and relentless touring. His storytelling style is cinematic and immersive — audiences don’t just laugh, they feel every word.
The Custom Fit Tour marks a major milestone for Siddiq: his first-ever arena show in Baltimore. Due to overwhelming demand, a second night was added at the Chesapeake Employers Insurance Arena — a testament to just how much his fanbase has grown.
Event Details
- Date: Sunday, May 24, 2026
- Doors Open: 6:00 PM
- Show Time: 7:00 PM
- Venue: Chesapeake Employers Insurance Arena
- Address: 1000 Hilltop Circle, Baltimore, MD 21250
- Phone: (443) 612-3840
- Content Warning: Mature themes and language — recommended for ages 18+
About the Venue
The Chesapeake Employers Insurance Arena, located on the campus of the University of Maryland, Baltimore County (UMBC), is one of Baltimore’s premier mid-size entertainment venues. With a capacity of approximately 5,000 for concerts and events, it offers an intimate yet energetic atmosphere that’s perfect for a high-energy stand-up comedy show.
The arena features excellent sightlines from virtually every seat, modern sound systems, and a welcoming layout that ensures every fan feels close to the action. Amenities include multiple concession stands, full bar service, and accessible seating options throughout the venue.
Parking is available on-site in the UMBC campus lots, and the venue is easily accessible via I-695 (Baltimore Beltway). The arena has hosted major concerts, sporting events, and comedy shows, making it a well-loved destination for Baltimore entertainment fans.
What to Expect
Ali Siddiq’s The Custom Fit Tour is a full-length headline stand-up comedy show. Expect an evening of powerful storytelling, laugh-out-loud moments, and the kind of authentic comedy that only comes from lived experience. Siddiq commands the stage with confidence and charisma, keeping audiences engaged from the first joke to the final punchline.
This is a solo headline performance — Ali Siddiq takes the stage and delivers a complete set designed to entertain, inspire, and leave you wanting more. The show typically runs approximately 90 minutes to 2 hours including any opening acts.
Fans of storytelling-driven comedy, fans of his Netflix specials, and first-time attendees alike will find this show to be an unforgettable night out in Baltimore.
Ticket Information
Price Range: $42.80 – $55.05 (official tickets, fees included) | Resale tickets from $63+
Official tickets are available through Ticketmaster. Resale tickets are available through VividSeats with the 100% Buyer Guarantee.
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All sales are final. Show times subject to change. Valid photo ID may be required for entry.